Windsor County Vacation Packages
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Your Windsor County Vacation
With a Windsor County vacation package, you can forget about planning hassles and instead focus on experiencing everything this exciting destination has on offer. Begin your trip to Windsor County with some time exploring Ludlow visiting popular sights like Weston Playhouse and Lake Rescue. Norwich is another top city that lures crowds from near and far. Quechee Gorge Bridge and Quechee Gorge Village are two of the leading places to see in this destination. From the instant you book your Windsor County vacation to the second you come back home, Expedia will take care of you each step of the way.
Top vacation destinations in Windsor County
Top Windsor County Vacation Deals
Price found within the past 48 hours. Click for updated prices.
Sinclair Inn Bed and Breakfast
CA $1,104
per person
Dec 6 - Dec 8
found 12 hours ago
Roundtrip non-stop flight included
Toronto (YYZ) to Springfield (VSF)
10/10 Exceptional! (127 reviews)
We had a wonderful stay at the Sinclair Inn Bed & Breakfast in Jericho, Vermont! The house is absolutely beautiful—a charming Queen Anne Victorian filled with character and historic charm. We stayed in Room 5 upstairs, which featured a comfortable king bed and a private bathroom. It was a lovely, comfortable place to relax and enjoy our visit.
Kyle, Holly, and their daughter Cassidy were amazing hosts! They went above and beyond to make us feel welcome. Earlier in our trip, before arriving at the Sinclair Inn, I had injured myself and was on crutches. When we arrived, Kyle graciously helped my wife carry our suitcases upstairs to our room. That thoughtful gesture meant so much to us and really showed the kindness and genuine hospitality of this wonderful family.
Breakfast was delicious, and one of the things we especially enjoyed was the opportunity to sit down, meet, and talk with the other guests. Those conversations added a personal touch to our stay and made the experience even more enjoyable.
Between the beautiful Victorian home, the comfortable accommodations, the delicious breakfast, and the outstanding hospitality, our stay was truly memorable. We highly recommend the Sinclair Inn to anyone visiting Vermont. If you're looking for a beautiful bed and breakfast with wonderful hosts who genuinely care about their guests, this is the place! We would absolutely love to stay here again.
Reviewed on Oct 18, 2026
Jackson Gore Village, A Vail Resorts Property
Jackson Gore Base Area
CA $6,838
per person
Dec 28 - Jan 3
found 1 day ago
Roundtrip flight included
Edmonton (YEA) to Springfield (VSF)
8.6/10 Excellent! (908 reviews)
I would suggest get there before it gets dark. The roads are very dark. No fault to the hotel at all just dark country roads.
Reviewed on Oct 18, 2026
Windsor County Hotel Deals
Woodstock Inn & Resort
Fourteen The Green Woodstock VT
CA $522
CA $636 total
Nov 16 - Nov 17
includes taxes & fees
Align Inn Vermont
5817 Woodstock Rd Quechee VT
CA $157
CA $173 total
Nov 1 - Nov 2
includes taxes & fees
9.4/10 Exceptional! (1,404 reviews)
"Clean good motel. Beds are very firm."
Reviewed on Oct 18, 2026
Jackson Gore Village, A Vail Resorts Property
111 Jackson Gore Road Ludlow VT
Fully refundableReserve now, pay when you stay
CA $262
CA $318 total
Oct 27 - Oct 28
includes taxes & fees
8.6/10 Excellent! (943 reviews)
"I would suggest get there before it gets dark. The roads are very dark. No fault to the hotel at all just dark country roads."
Reviewed on Oct 18, 2026
Lowest nightly price found within the past 24 hours based on a 1 night stay for 2 adults. Prices and availability subject to change. Additional terms may apply.
Frequently asked questions
How much does a Windsor County vacation package cost?
Choose from any combination of hotels, flights and car rentals, and you can be vacationing in Windsor County from just CA $1,104. And the more you bundle, the more cash you save. The vacation of your dreams has never been more affordable.
How do I get a cheap travel package to Windsor County?
You'll save a ton of money if you bundle your hotels, car rentals and flights into a Windsor County travel package. Sometimes cheap packages mean fewer choices. But not with Expedia. We offer over 550 airlines and 1,000,000 hotels all over the world, which means you'll always have plenty of variety to choose from. Want to save even more? Add some exciting activities to your package deal to unlock even more bargains! After all, travel is about more than simply getting to your destination.
Where should I stay in Windsor County?
Okemo Mountain Resort is one of the key things that lures people to Windsor County, so it makes perfect sense that many decide to book their hotel in Ludlow.
What are the top hotels in Windsor County?
When it comes to hotels in Ludlow, Super 8 by Wyndham White River Junction and Holiday Inn Express Hotel & Suites White River Junction, an IHG Hotel are two terrific options. If you're spending time in Plymouth, Hotel Coolidge and White River Inn and Suites will make you feel right at home.
How far in advance should I book my Windsor County vacation?
It depends on the airline, but you can usually browse through international fares on Expedia up to a year in advance. While it's advisable to book ahead of time, lucky customers will sometimes find a cheaper flight only weeks before their intended journey.
What does an Expedia Windsor County travel package include?
It comes down to what you're looking for. If you're traveling by yourself, you might decide to bundle hotels and flights. Bringing the entire family to Windsor County? A travel package that includes hotels, rental cars and flights might suit you better. Expedia gives you the freedom and flexibility to tailor your travel package.
What should I know before booking a Windsor County travel package?
You'll save big with an Expedia travel package. Combine your flights, rental cars and hotels and be rewarded with great discounts. Hotels aren't your only choice, however. Book with us and take your pick of beachside condos, chalets in the middle of mountains and even glamping tents!
Can I choose my airline with a Windsor County Expedia vacation package?
Most definitely. Expedia has more than 550 partner airlines to select from across the world. With so many choices, finding the ideal carrier to fly you to Windsor County will be a snap.
If I'm not able to travel, can I cancel my Windsor County vacation package?
We get it — unexpected stuff happens. If you've locked in a Windsor County vacation package and need to amend or cancel it, we can help. It's always worth browsing our Customer Service Portal first for information. But generally, if you've booked your package within 24 hours, you may be able to amend or cancel your itinerary free of charge. If it's been more than 24 hours, your hotel, airline or car rental company may impose a charge.
Stay near popular Windsor County attractions
Okemo Mountain Resort
9.2/10 (510 reviews)
Hit the slopes in Ludlow with a visit to Okemo Mountain Resort. Discover the mountain views in this romantic area.
Photo by Mike Gauthier
Quechee Gorge Bridge
9.2/10 (580 reviews)
Quechee Gorge Bridge is just one of the places to see in White River Junction, so why not enjoy the other things to explore during your travels? Wander the riverfront in this quaint area.
Photo by George Sykes
King Arthur Baking Company
9.4/10 (178 reviews)
You can enjoy retail therapy at King Arthur Baking Company during your stay in Norwich. While you're in the area, stroll along the riverfront.
Photo by Ed Gaffny
Quechee Gorge Village
9.0/10 (288 reviews)
You can enjoy retail therapy at Quechee Gorge Village during your trip to Quechee. Amble around the area's riverfront or seek out the ski slopes.
Photo by William E Berry Jr.
Mount Ascutney
8.8/10 (27 reviews)
Commune with nature and explore the great outdoors at Mount Ascutney during your travels in Brownsville. You can seek out the ski slopes while in the area.
Billings Farm and Museum
9.2/10 (84 reviews)
You can study the exhibits at Billings Farm and Museum, a museum with a storied past, during your trip to Woodstock. Wander the riverfront in this quaint area.
Simon Pearce Mill
9.0/10 (80 reviews)
Learn about the local history of Quechee when you spend time at Simon Pearce Mill. Amble around this family-friendly area's riverfront and enjoy its top-notch restaurants.
* Savings based on package bookings compared to the price of the same components booked separately. Savings not available on all packages.
